Ammonium iodide → HCID 58423951, compound

HRID 1408576Notes

Reaction equation

HRID 1408576 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[N:14]([CH3:17])[C:13](SC)=[N:12]3)[CH2:10][CH:9]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH4+:25].[I-].N.CCO>>[NH2:25][C:13]1[N:14]([CH3:17])[C:15](=[O:16])[C:11]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[O:8][CH:9]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH2:10]2)[N:12]=1

Participants

4

Reactant 3

HCID 25487Ammonium iodideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 58423965HCID 58423965, compound

Product 1

HCID 58423951HCID 58423951, compoundYield 27.1%

Procedure

A solution of 6-bromo-1′-methyl-2′-(methylthio)-2-(thiophen-2-yl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.047 mmol), NH4I (13.7 mg, 0.094 mmol) in a solution of NH3/EtOH (2 mL, 2 N) was heated at 110° C. in a tube in a microwave reactor for 2-2.5 h. After cooling, the mixture was concentrated in vacuum to give the residue, which was purified by preparative TLC to afford 2′-amino-6-bromo-1′-methyl-2-(thiophen-2-yl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (5 mg, 20%). 1H-NMR (CDCl3): 2.52 (m, 2H), 3.14 (s, 3H), 6.12 (d, 1H), 6.94 (d, 1H), 7.02 (t, 1H), 7.14 (d, 1H), 7.43 (t, 3H).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuum
  3. customto give the residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-cf6dbc6081b54a39afb2ae4518db6e64
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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